Windsor County Vacation Packages
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Your Windsor County Vacation
With a Windsor County vacation package, you can forget about planning hassles and instead focus on experiencing everything this exciting destination has on offer. Begin your trip to Windsor County with some time exploring Ludlow visiting popular sights like Weston Playhouse and Lake Rescue. Norwich is another top city that lures crowds from near and far. Quechee Gorge Bridge and Quechee Gorge Village are two of the leading places to see in this destination. From the instant you book your Windsor County vacation to the second you come back home, Expedia will take care of you each step of the way.
Top vacation destinations in Windsor County
Top Windsor County Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Brookside Hideaway, Brook Road Inn
CA $958
per person
Oct 10 - Oct 12
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Lebanon (LEB)
10/10 Exceptional! (1 review)
This is a secret Hidaway. Don't judge a book by its cover. Very cozy, roomy cottage. We were a family of 4 and there was more than enough room. Communication was amazing and is what made our stay easy!
Perfect distance to Mount Sunapee.
Reviewed on Feb 21, 2025
Hideaway Inn Mt. Snow
CA $1,463
per person
Oct 10 - Oct 13
found 17 hours ago
Roundtrip flight included
Calgary (YYC) to Springfield (VSF)
8.6/10 Excellent! (128 reviews)
This was the perfect long weekend get away. The property was fairly quiet given it was the off season. Phone check-in and check-out was lovely, and if you don’t enjoy standard hotel check-in lines, it’s even better. The pool and hot tub were beautiful, and while we didn’t use them, they were very clean. It is a very pet friendly place, but doesn’t smell of animals, and there’s no sign of them (unless you meet one in the hallway). The always available hot chocolate and coffee machine was AMAZING! Highly recommend the hot chocolate.
We only saw the cleaner once in passing (they don’t go in your room while you’re there), and she was so nice! There’s also extra supplies for you in the main hall closet should you need them (extra towels, tooth brushes, etc.).
It truly felt like a home away from home. The only “downside” is that the walls are a bit thin so you can kind of hear what your neighbors are doing if they’re being rowdy, but that’s more managing personal volume levels.
10/10, we’ll definitely stay again!
Reviewed on Sep 8, 2026
Mount Snow Lodging by Vail Resorts
CA $1,753
per person
Oct 10 - Oct 13
found 17 hours ago
Roundtrip flight included
Calgary (YYC) to Springfield (VSF)
7.8/10 Good! (23 reviews)
The bar tender in the lounge on Saturday 10/18 was not friendly. Seemed like he didn’t like his job. He was the only one working and there were not many customers at the bar. Dining room had no one in it. He just was not attentive to me party of 3 who just wanted to order a drink. Fitness center at the Season was very nice but hours were not very accommodating
Reviewed on Oct 20, 2025
Mountain Lodge at Okemo, A Vail Resorts Property
Clock Tower Base Area
CA $1,441
per person
Oct 10 - Oct 13
found 17 hours ago
Roundtrip flight included
Calgary (YYC) to Springfield (VSF)
8/10 Very good! (225 reviews)
Staff was very helpful, the property is very clean, the room was clean with lots of space. The kitchen had a full size refrigerator and microwave. I was very happy overall
Reviewed on Jul 19, 2026
Windsor County Hotel Deals
Align Inn Vermont
5817 Woodstock Rd Quechee VT
CA $138
CA $152 total
Sep 13 - Sep 14
includes taxes & fees
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
CA $729
CA $863 total
Sep 14 - Sep 15
includes taxes & fees
9.4/10 Exceptional! (604 reviews)
"I wouldn’t run back here. It’s a nice hotel in general. The gardens are pretty. Downsides are the facility’s. Outdoor pool area is average. Looks run down. There is no onsite indoor pool, gym, sauna etc , this is over 1 mile away and also is currently under construction. Breakfast was poor for a ..."
Reviewed on Sep 9, 2026
The Jackson
43 Senior Lane Woodstock VT
CA $406
CA $447 total
Sep 16 - Sep 17
includes taxes & fees
9.6/10 Exceptional! (314 reviews)
"The inn and the grounds are beautifully maintained. The room was comfortable, and the restaurant on the premises was convenient but also had a great breakfast, well worth purchasing. The location was also great relative to downtown."
Reviewed on Sep 6, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Frequently asked questions
How much does a Windsor County vacation package cost?
Choose from any combination of hotels, flights and car rentals, and you can be vacationing in Windsor County from just CA $958. And the more you bundle, the more cash you save. The vacation of your dreams has never been more affordable.
How do I get a cheap travel package to Windsor County?
You'll save a ton of money if you bundle your hotels, car rentals and flights into a Windsor County travel package. Sometimes cheap packages mean fewer choices. But not with Expedia. We offer over 550 airlines and 1,000,000 hotels all over the world, which means you'll always have plenty of variety to choose from. Want to save even more? Add some exciting activities to your package deal to unlock even more bargains! After all, travel is about more than simply getting to your destination.
Where should I stay in Windsor County?
Okemo Mountain Resort is one of the key things that lures people to Windsor County, so it makes perfect sense that many decide to book their hotel in Ludlow.
What are the top hotels in Windsor County?
When it comes to hotels in Ludlow, Super 8 by Wyndham White River Junction and Holiday Inn Express Hotel & Suites White River Junction, an IHG Hotel are two terrific options. If you're spending time in Plymouth, Hotel Coolidge and White River Inn and Suites will make you feel right at home.
How far in advance should I book my Windsor County vacation?
It depends on the airline, but you can usually browse through international fares on Expedia up to a year in advance. While it's advisable to book ahead of time, lucky customers will sometimes find a cheaper flight only weeks before their intended journey.
What does an Expedia Windsor County travel package include?
It comes down to what you're looking for. If you're traveling by yourself, you might decide to bundle hotels and flights. Bringing the entire family to Windsor County? A travel package that includes hotels, rental cars and flights might suit you better. Expedia gives you the freedom and flexibility to tailor your travel package.
What should I know before booking a Windsor County travel package?
You'll save big with an Expedia travel package. Combine your flights, rental cars and hotels and be rewarded with great discounts. Hotels aren't your only choice, however. Book with us and take your pick of beachside condos, chalets in the middle of mountains and even glamping tents!
Can I choose my airline with a Windsor County Expedia vacation package?
Most definitely. Expedia has more than 550 partner airlines to select from across the world. With so many choices, finding the ideal carrier to fly you to Windsor County will be a snap.
If I'm not able to travel, can I cancel my Windsor County vacation package?
We get it — unexpected stuff happens. If you've locked in a Windsor County vacation package and need to amend or cancel it, we can help. It's always worth browsing our Customer Service Portal first for information. But generally, if you've booked your package within 24 hours, you may be able to amend or cancel your itinerary free of charge. If it's been more than 24 hours, your hotel, airline or car rental company may impose a charge.
Stay near popular Windsor County attractions
Okemo Mountain Resort
9.2/10 (510 reviews)
Hit the slopes in Ludlow with a visit to Okemo Mountain Resort. Discover the mountain views in this romantic area.
Photo by Mike Gauthier
Quechee Gorge Bridge
9.2/10 (580 reviews)
Quechee Gorge Bridge is just one of the places to see in White River Junction, so why not enjoy the other things to explore during your travels? Wander the riverfront in this quaint area.
Photo by George Sykes
King Arthur Baking Company
9.4/10 (178 reviews)
You can enjoy retail therapy at King Arthur Baking Company during your stay in Norwich. While you're in the area, stroll along the riverfront.
Photo by Ed Gaffny
Quechee Gorge Village
9.0/10 (288 reviews)
You can enjoy retail therapy at Quechee Gorge Village during your trip to Quechee. Amble around the area's riverfront or seek out the ski slopes.
Billings Farm and Museum
9.2/10 (84 reviews)
You can study the exhibits at Billings Farm and Museum, a museum with a storied past, during your trip to Woodstock. Wander the riverfront in this quaint area.
Photo by William E Berry Jr.
Mount Ascutney
8.8/10 (27 reviews)
Commune with nature and explore the great outdoors at Mount Ascutney during your travels in Brownsville. You can seek out the ski slopes while in the area.
Simon Pearce Mill
9.0/10 (80 reviews)
Learn about the local history of Quechee when you spend time at Simon Pearce Mill. Amble around this family-friendly area's riverfront and enjoy its top-notch restaurants.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
